Reference of 2606-51-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2606-51-1, name is 5-(Bromomethyl)benzo[d][1,3]dioxole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
A solution of 3 (870 mg, 3.36 mmol) in DMF (8 mL) was treated with 60% NaH dispersion in mineral oil (134 mg, 3.36 mmol) under N2. The mixture was stirred at r.t. for 10 min, then 4-(bromomethyl)-1-fluoro-2-methoxybenzene (700 mg, 3.20 mmol) was added. The resulting mixture was stirred at 20 C under N2 for 2 h. The mixture was diluted with H2O (80 mL) and extracted with EtOAc (80 mL). The organic layer was dried (MgSO4), filtered and evaporated. The crude product was purified by flash silica gel chromatography (eluent: gradient 20 to 25% EtOAc in heptane). Pure fractions were evaporated to dryness and dried under high vacuum to afford the title compound 4, containing 32 mol% EtOAc (1.20 g, 88%, allowing for solvent residues) as a colourless oil. 1H NMR (500 MHz, CDCl3): delta = 7.73 (d, J = 8.1Hz, 2 H), 7.31 (d, J = 8.1Hz, 2 H), 6.96 (dd, J = 11.1, 8.2 Hz, 1H), 6.82 (dd, J = 8.2, 2.1Hz, 1H), 6.71 (ddd, J = 8.2, 4.2, 2.1Hz, 1H), 4.42 (s, 2 H), 4.36 (t, J = 5.3 Hz, 1H), 3.78 (s, 3 H), 3.26 (s, 6 H), 3.21 (d, J = 5.3 Hz, 2 H), 2.43 (s, 3 H). 13C NMR (126 MHz, CDCl3): delta = 151.9 (J = 245.6 Hz), 147.7 (J = 11.0 Hz), 143.4, 137.5, 132.6 (J = 3.7 Hz), 129.7, 127.2, 120.9 (J = 6.8 Hz), 115.7 (J = 18.5 Hz), 113.4 (J = 1.7 Hz), 104.0, 56.1, 54.7, 52.3, 48.8, 21.5. MS (ES+): m/z = 334 [M + H – 2 MeOH]+. [CAS Reg. No. 1036711-00-8] A solution of 4 (1.18 g, 2.96 mmol) in 1,4-dioxane (12 mL) was treated with 6 N aq HCl (3.94 mL, 23.7 mmol) under N2. The resulting mixture was stirred under vigourous reflux for 24 h. The mixture was evaporated and the residue partitioned between EtOAc (50 mL) and 0.1 M aq NaHCO3 (70 mL). The aqueous layer was extracted with EtOAc (70 mL) and the extracts combined with the organic layer. The combined organic extracts were washed with sat. brine (50 mL), dried (Na2SO4), filtered and evaporated. The crude product was purified by flash silica gel chromatography (eluent: gradient 20 to 50% EtOAc in heptane). Pure fractions were evaporated to dryness to afford the title compound 17 (376 mg, 72%) as a beige solid
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-(Bromomethyl)benzo[d][1,3]dioxole, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Pearson, Stuart E.; Fillery, Shaun M.; Goldberg, Kristin; Demeritt, Julie E.; Eden, Jonathan; Finlayson, Jonathan; Patel, Anil; Synthesis; vol. 50; 24; (2018); p. 4963 – 4981;,
Bromide – Wikipedia,
bromide – Wiktionary